(YOOO Requested by Pika_Puff  yo, you are very kind and I loved your request. Thank you for requesting! If there need to be any changes, let me know <3

♡S/O Headcanons♡ - Reader is female)

---

☆~ Keith (Bf)

-When you announced that your parents allowed you to sleep over at Keith's house, he was surely happy. Your parents adore him, despite thinking he was a drug dealer when first meeting him.

-He is the perfect place to go if your parents are strict over your diet. He will give you anything from ice cream pops or order pizza for you if you wish. He knows full well you have anxiety when ordering food.

-The two of you would rap battle at night and play plenty of video games, a lot of them consist of Guitar Hero, any Wii game, and surprisingly, Beat Saber on his headset. He doesn't own many headset games since they can be costly but it's still a nice addition.

-You two will be up a lot and make fun of kids on Roblox at 1 am. Any online mobile game and you two will always laugh at kids.

-When you don't want to play any more games, you both watch YouTubers playing video games or watch comedy on Netflix. It was awkward adjusting at first, but you two eventually found a rhythm where you would watch a movie together and fall asleep.

-His pajamas are quite simple. He likes to wear baggy pants but remains shirtless. For someone who eats a lot of junk food, he seems to have a high metabolism since he has a lean body.

-He is very grabby and demanding of your attention if you stare at your phone for too long. He would make excuses and demand kisses on his cheek. "Penalties" as he calls them.

-"Oh! Penalty for being on your phone for five minutes! Time to kiss me five times."
"I was just trying to text my mom/dad-"

---

☆~ Gabby (Gf)

-She is your typical girl whenever it comes to sleepovers. She will talk about so many guys but she will also talk about Girl in Red or Conan Gray with you.

-If you wear make-up, one of her favorite things is giving you a new look or trying something that you haven't tried before. Sometimes, the two of you will laugh and other times, it looks really good. For the fun of it, you would put blindfolds on each other and do each other's make-up.

-She's the type of simple girl who would put on a lofi mix playlist and play Uno with you. She will do anything, such as playing card games (funny enough, her favorite game is Poker), taking selfies with you, or handing you all of her attention.

-She loves making you feel special, so she will hold you close, kiss your forehead, and play with your hair all night long. She's not the type to go for horror movies, so you always settle with some drama-related movie or show.

-When she gets playful or wants your attention, she will make you sit on her lap. You always get embarrassed by this since you cannot deny that her lap (and thighs in general) is a comfortable spot. It's even more embarrassing when her parents spot you two.

-Lastly, her pajama set makes you want to fall for her over and over again. Her pajamas are the My Melody pink bunny set, and holy hell does she look extremely hot in it. She encourages you to try the white set, sometimes you do wear it... other times you are very shy.

---

☆~ Pico

-Your parent/s had to get a lot of convincing for you to get a sleepover at Pico's. After a lot of time, that day finally came and Pico wanted to make sure it was going to be epic since it's hard getting a sleepover at his place.

-One of the first things you two did was spray paint in his garage and admire his huge dog. A Great Dane and German Shepard mix named Max. His parents are quite laid back (you aren't even surprised if one of them smoked some sort of pot) and they honestly didn't care what the two of you did.

-He taught you how to carefully handle a bb gun and gave you practice targets. It was more fun than you expected. He got nervous one time and decided to make you switch out the bb gun for a paint gun. You had to reassure him that you are responsible, more responsible than him in fact.

-The two of you tag teamed on making dinner, which had a lot of cookies and homemade tacos involved. You were thankful that a food war didn't break out between you two, but it became very close.

-"Put down the tomato slices and I'll put down the lettuce!"
"No! Put down your lettuce first, then I will set down the tomato slices."

-Despite Pico not living in the safest neighborhood, with a trailer park as his neighbor, you somehow felt secure around him. You can't tell if it's all the guns or his chill parents, or maybe his need to constantly check up on you, but you had some security.

-Depending on what time, he will be shirtless. During the taco making, his kitchen got increasingly hot and he took off his shirt. The only remaining thing on him were cargo shorts and a dog tag necklace. He literally looks like a young adult who entered the military.

-Your face got hotter than the oven when he took off his shirt and you tried to dismiss it constantly. He kept asking if you were sick. He eventually caught on and tried to flirt with you.

-You were so tired by the end of the night, you crashed on the couch in their living room. He shortly joined you and you two had a cuddle fest. Max even joined the two of you and you two had to constantly push the dog off since he crushed you both.

---

☆~ Skid and Pump

-They knew the day was coming. Whether it was the countless times they bugged your parent/s or you had to desperately tell your mom and/ or dad yourself that you wanted to spend time with them, the day finally came.

-The look on their faces was pure. The two teenagers were so happy and they wouldn't be quiet about the dang sleepover until it actually came.

-They waited by the door desperately to watch when you will come up in the driveway. They welcomed you almost instantly. The two gave you the fastest tour of humankind that you have ever seen because they wanted to jump right into the fun.

-You three played numerous games and their mom, a lady with long purple hair, would join on some. She was fun but you can tell that you don't want to get on her bad side. Luckily, she adores you a lot.

-Of course, one of their favorite games is Just Dance on the Wii. They only pull one move and it's the Spooky Month dance move and surprisingly, they get some good points on Just Dance. They have enough controllers for the three of you, so while you dance to the character on screen, these two do their random dance.

-There will be constant debates (the grand majority are playful) between the two and you would always be chosen to be the deal-breaker. You try to even it out. In some debates, you choose Pump's choice, and other times it's Skid's.
"I want to play Twizzler, but he wants to go outside! What should we do, Y/n?!"
"U-Uh... outside... Twizzler?"

-When you accidentally seemed stressed or awkward about asking for something, the two will not stop kissing your cheeks. Skid will deliver one on your right, Pump will then do one on your left. They will keep doing this until you laugh. If you get more embarrassed, they will only keep doing it.

-You were thankful that their mom prepared food instead of you having to choose an option or making it yourself. You know damn well these two will burn the house down if they make something as simple as Mac N Cheese.

-Finding a location to sleep was something that isn't easy. The two wanted to be close to you but there aren't many options that can do that. For you, it's more of wherever you crash at, you crash there and they will have to figure it out.

-Funny enough, you ended up falling asleep on the floor while watching a movie. The two did everything from putting a pillow under your head to giving you an extra blanket so you don't freeze. At least they got to snuggle beside you without having any issues with someone falling off the bed or couch.

---

☆~ Witty

-You don't know Witty's parents well enough, neither do your parent/s. You told your mom and/or dad that you had a school poster board you had to make with Witty that was due after the weekend. So, your parents decided to let Witty spend the night. They felt more comfortable with him coming over than you going over, and you weren't going to argue with that.

-He didn't speak much besides giving some simple greetings and paying respect to your parent/s. They have mixed feelings over him. If you trust your parent/s enough to tell them that you are dating him, they would question why you like him in the first place. It's rude, you are well aware.

-He doesn't like eating in front of many people, especially people he doesn't know well enough. You two would stay in your room for a lot of the night.

-Making the poster is hard since you both keep distracting one another. You would smear his face with a paintbrush and he would toss a pile of glitter at you in return. It ended up in a bunch of laughter. Your room became a mess but he's kind enough to offer some help to clean. You, of course, declined.

-You didn't care how pretty the poster was, as long as you spent time with Witty, you were happy.
"The crabby science teacher can suck it anyway." Witty will comment.

-One of the times he went to the bathroom, he left his hoodie in your bedroom. You never have been so fast to snatch it up and put it on. He didn't even notice at first. He walked into your bedroom, looking for his hoodie only to realize that you are wearing it with a smug smile on your face.

-"Y/nnn, you are going to get glitter all over it."
You refuse to take it off and after some complaining, he knew that you wouldn't budge.

-You sometimes forget how clingy and cuddly Witty can be. He would always ask for consent, of course, but once he latches onto you, you are stuck in a cage. He specifically likes the position where he is hugging you from behind, face tucked into your nape and legs around your waist.

-At the end of it all, he will hold you closely until you fall asleep. He likes listening to your heartbeat and you like it when he trails little shapes on your back with his finger. He is far taller than you and you feel exceptionally safe whenever you are close, which brings you into a nice sleep.

---

☆~Daddy Dearest and Mommy Mearest

⚠️Trigger warning: Parents kick Y/n out of the house. This isn't a significant other headcanon but rather a parent/daughter bond⚠️

-This was a strange sleepover, to say the least. Your mom and/or dad kicked you out of the house out of anger when a massive fight broke out. They thought you are old enough to sustain yourself when clearly you are not.

-The next reliable option was to go to Mommy Mearest and Daddy Dearest, it was luckily an option that you thought of quickly. The two absolutely adore you and they were quick to invite you into their home when they heard about the situation.

-Crying all night long? It's prone to happen but the two will do everything to make you feel better. Bake cookies, sing your favorite song, watch your comfort show with you, pull off a fake fashion show- literally anything. Hell, Gabby would join in and try to make you feel better. Most of the time, they did a fantastic job in distracting you from reality.

-They gave you your space whenever they felt that you needed it. They give you a bunch of plushies, ranging from adorable Squishmellows to cute Japanese sushi rolls. These two are the best at comforting you and presenting you with goodies. They also hand out good advice and solutions in case a situation happens.

-You slept for a long time and they were still eager to give you anything the next morning. By then, you felt much better but of course, they handed you a lot of pancakes/waffles/bacon, whatever breakfast food item of your choosing.

---

☆~ Takeda (Senpai)

-He is very charming, outgoing, and funny to a lot of people, especially to your mom and/or dad. Your parent/s liked him almost immediately. You are extremely relieved that he is likable in your family, so getting a sleepover wasn't too much of a hassle.

-His parents are nice to you and you were so awkward when meeting them. You have a feeling you and his parents will be great friends, but for now, you are stuck in the awkward valley.

-You and Takeda make fun of a lot of dating simulator games together. Two games you played together were Dream Daddy and Obey Me, but Takeda got jealous when he noticed you were beginning to fancy one of the demons from the second game. You both constantly laugh at each other.

-"Takeda, you look like the younger, skinny version of Joseph from Dream Daddy."
"Hush, at least I'm not in love with a white hair tan demon who constantly wants to steal your credit card information."
"Listen here you little shi-"

-You two talk a lot and hardly go on your phone. Even if he glances at his phone, you say something very quickly or quietly to get his attention. Most of the time, he doesn't hear and you laugh. Other times, when he does hear it, he gets very flustered.

-"You know, my throat is sort of bored at the moment, wink wink."
"Y/n, did you say something?"
"I said my boat is getting mowed at the moment, blink blink."
"Th-That is not what you said-"

-He has a chonky calico cat named Whiskers and you are extremely in love with her. Whiskers loves you so much as well and she will lay on your lap despite being a bigger cat. She has a loud purr and she is the perfect distraction for when Takeda has to go to the bathroom or such. Not to mention, she is extremely fluffy too.

-You both are a tingle of limbs when going to sleep. You try to cuddle but then it gets too hot, or Whiskers will get in the way, or his parents will interrupt you.

-Either way, trying to get some peaceful sleep and cuddles at the same time is a struggle. At one point, he said he had to go to the bathroom but you were convinced you accidentally gave him a... something you'd rather not say. Oh boy, you wouldn't stop apologizing and he worriedly tried to reassure you that he's fine.

---

☆~ Lemon Demon

-Technically, you have a sleepover with him every night since he practically lives in your closet. Either way, he makes an exception to like you and you only, which is a relief since you know he won't eat you.

-You two stay in the dark for the majority of the night, and whenever you wanted light, you would flick your phone's flashlight on or turn on fairy lights. It was easy on your eyes and you are content with the low lighting.

-If you cry any night, he will offer to eat a child for you. Does it make you feel better? Nope, but you are thankful that he thinks about you often. He doesn't entirely know how to comfort you on certain days. You have such a strange dynamic with him, he is an odd demon after all.

-One thing he does is engage in deep conversations with you in hopes to hear you talk. He likes your voice a lot. This demon would ask you questions, such as "Does solid matter exist if molecules vibrate?" And "What do you believe the purpose of life is?" You both have very different answers but hearing each answer is intriguing.

-If you are bored, you share some music tastes with him and open your laptop to the Spotify browser. That way, he can see all of your playlists, music type, and experience other music of his own.

-He has a struggle typing on the keyboard so you often have to help him out. Hell, you even made a playlist of the songs he prefers. A lot consists of a mixture of dream core and metal.

-Depending on your mood, he will join you when you go to sleep. He really likes your warmth and will hold you close. You cannot deny that he has a lovely voice and sometimes it can lull you to sleep. He doesn't sing about eating anyone when he sings to you, but rather hums.